反应详情

A round-bottomed flask was charged with 2-iodoisonicotinic acid (0.70 g, 2.81 mmol), HOBt (474 mg, 3.09 mmol) and EDC (593 mg, 3.09 mmol). DMF (4 mL) was added followed by methylamine (2.0M solution in THF, 8.0 mL, 16.0 mmol) and the resultant suspension was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted with 70 mL diethyl ether (2×). The combined organic layers were washed twice with ˜5 mL water and once with ˜5 mL brine then dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over 24 g silica gel with EtOAc/Hexanes (gradient: 0-60% EtOAc). All fractions containing product were combined and concentrated to give 410 mg (56%) of 2-iodo-N-methyl-isonicotinamide as a white solid.

1. customThe reaction mixture was quenched with water
2. extractionextracted with 70 mL diethyl ether (2×)
3. washThe combined organic layers were washed twice with ˜5 mL water and once with ˜5 mL brine
4. dry with materialthen dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was chromatographed over 24 g silica gel with EtOAc/Hexanes (gradient: 0-60% EtOAc)
8. additionAll fractions containing product
9. concentrationconcentrated